Which Girl?
by blakewillams99
Summary: After his lost in the Kalos League, Ash gains a new girlfriend in Serena, there relationship is going fine, that is until Ash returns home, where an old friend is staying and soon a old crush reemerges and Ash is now torn between on Serena and May, Which girl will Ash choose? Advnaced vs Amour (Rated M for Lemons in later chapters)
1. A Surprise

Pokemon Which Girl? Chapter 1 A Surprise

Ages

Ash-18

Serena-17

May-17

Clemont-18

Ash had just lost in the Kalos League and he was sad and disappointed by the lost, as yet again he lost in another league, For a few days after the lost Ash just moped around, but he cheered up by his new girlfriend Serena, who had confessed her love for Ash, and the couple along with Serena and Clemont and Bonnie, where currently heading to Ash's childhood home.

Once arriving at his home, Ash knocked on the door, where he was greeted by a big hug from his mother "Ash missed so much" She said while enveloping her son into a huge.

"I missed you to mom" He said muffled voice.

Delia then turned her attention towards Ash's childhood friend, now girlfriend Serena "Hello Serena, thanks for taking care of my boy for me" She said to her.

Serena blushed "Your welcome Mrs. Ketchum" She replied.

Delia then in and Ash was shocked to see who was on the couch "May" He said in shock.

"Ash it's so good to see you" She said jumping off the couch and giving her old friend in a hug.

Serena looked in jealousy, as Ash had mentioned May a bunch of time before, In face more than his other friends and to add to the fact she was stunning. The two friends separated from the long hug and the got a good look at each other. Ash took a look a May and she had gotten even more beautiful, as her hair gotten longer, Ash knew that May had developed breasts at a young age and since it had been a couple of years, they had gotten bigger and they looked to be around a D cup, maybe even a double DD, She had an amazing figure that any girl would dream of, She a big butt to go along with her nice legs and curves, Overall she had an amazing body that guys drooled over and girls would envy, including his own girlfriend.

"Wow May you look so beautiful" He said as secretly checked out her body.

May blushed "Thanks Ash, you look quite handsome yourself" May said.

Ash blushed as Serena let out a small huff, May then turned her attention to Ash's new friends and girlfriend "Hey I'm May" She cheerfully greeted them.

"Hey I'm Serena" Serena replied with a fake smile.

"Hey I'm Bonnie and this big brother Clemont" The cute little girl said.

May smiled and giggled at the cuteness of the little girl "Nice to meet you all" May said in a cheerful tone.

"Not to be rude, but what are you doing here?" Ash asked his friend.

"Well, to be honest, I've been missing you Ash" She said.

"I've missed you to May" He replied.

Serena gave a glare to May, as she was making it seem like she wanted her boyfriend.

All of them then sat down on the couch, as May and Ash shared old stories of each other and learned what they had done, Ash learned that May was now accomplished coordinator, as she had won 2 grand festivals and was currently on her 3rd, Clemont and Bonnie immediately feel in love with May's bubbly personality, as it was really hard for anyone to dislike May, as she such a sweet and caring person that could get along with about anyone.

Well besides Serena, as she was getting more and more jealous by the second, as it was May getting all the attention, even from her boyfriend as she could feel her anger rising, Unknown to Serena though, May was actually trying to her get her boyfriend, all she wanted to see is an old friend, She has to admit though she use to have a big crush on Ash, but since learning of Ash and Serena's relationship, she put the crush behind her.

"Dinner's ready" Delia shouted from the kitchen.

May and Ash quickly ran into the kitchen, at the mention of dinner, and they quickly pilled up a plate full of food that Delia had made, Soon the rest made their plates and soon May and Ash dug into the delicious dinner, as Serena, Clemont, and Bonnie looked on in shock, as they thought they would never seen someone, especially a girl, match Ash's appetite.

It taken long for May or Ash to finish their dinner as both of them let out a loud burps in unison, Serena could feel herself getting even more jealous as they seem to have so much in common. "That was great mom" Ash said with his stomach full.

"Yeah that was great Delia" May agreed with Ash.

"Well, thanks" She replied.

The rest of the day was spent was telling old and new stories between Ash and May, with Serena mostly being left out. It was now night time and everyone was getting ready for bed, as Ash and Serena would be sleeping in Ash's room together, while May would be sleeping in the guest room, Bonnie and Clemont would be sleeping downstairs on a air mattress.

May had offered to sleep downstairs on the air mattress, but Bonnie and Clemont insisted on her sleeping upstairs in the guest, it took some arguing, but May finally gave in. May had just changed into her sleeping attire and she decided to tell Ash good night, She went to his bedroom door and knocked on the door "Come in" She heard Ash's voice say.

May opened the door as Serena immediately shot her glare on sight of her "I just wanted to tell you goodnight Ash" She said.

"Well night May, I'm glad you decide to stop by" He said.

Serena rolled her eyes as May blushed "I am too, I missed you so much Ash" She said wrapping her best friend into a hug.

Ash accepted the hug and huge smile formed on his face, Meanwhile Serena continued to glare at her, The hug lasted a long time, as the two friends missed each other dearly, maybe too long in Serena's opinion "Alright night Ash, night Serena" She said to the couple.

"Night May" They both said.

While May was leaving, Ash couldn't help but stare at her big butt bouncing in her pajamas shorts that she was wearing, as she exited the room and Ash could feel his dick hardened in his boxers, Ash felt ashamed, as not only did he looked at his best friend's butt, but he also did in front of his girlfriend, Ash never looked at a girl's butt, But May's butt was so amazing and big, it was probably the biggest butt he had ever seen.

As Ash turned his head around, His girlfriend shot him a glare, Seeing the act earlier and from the fact of their interactions from earlier in the day "What?" Ash asked confused.

"Nothing" She replied.

Ash then crawled into bed with his girlfriend, as the couple cuddled together, with both of them falling asleep.


	2. Talk

Pokemon Which Girl? Chapter 2 Talk

Later That Night

May had been trying to go asleep for a couple of hours now, but she just couldn't just fall asleep, as she was thinking about Ash, To be honest earlier in the day when she first saw Ash with Serena, It broke her heart. As mentioned before, May had gotten over her crush over Ash, but seeing Ash today reignited her love for Ash. She was putting on act, as she just wanted to see Ash happy and Serena seemed nice and she treated Ash nicely.

But she wanted Ash so bad, but she would try to push aside her recently returned crush for Ash and Serena, so they could have a happy relationship. As she thought about Ash and some old memories of them, she could feel some tears trickle down her face, she quickly wiped them away.

Knowing that she couldn't fall asleep, May got out of bed and went outside to look at the night sky, She went to a cliff, where she got an amazing view of all the stars out and she began to stare at the stars, reminiscing about old memories of her and Ash.

Meanwhile in Ash's Room

Ash had just woken up and he had just had a wet dream about May and he breathed heavily, as he didn't know why he had a wet dream about her and felt bad, as not only was about his best friend, but he also had a girlfriend. Ash deiced to get out a bed and grab something to drink, so he went into the kitchen and quickly downed a cup of water. When walked back to his room. He looked out the window and saw a figure looking at the stars and he quickly recognized it to be May, He went outside and sat down by her and he looked at her and she looked even more beautiful than usual, as the night sky made her look more beautiful "Hey May what are you doing out here?" Ash asked her.

"I was just thinking about old times" She replied.

Ash smiled as she began to think about old times "I miss it too May" He said.

She looked over at Ash and blushed "How's Max doing?" Ash asked her.

She giggled softly "He's doing great, you know becoming the next Pokemon Master" She said while gigging.

He chuckled as well "That's awesome" He said.

May looked over at Ash as a few more tears trickled down her beautiful face "You know Ash I missed you a lot" She said to him.

Ash looked deeply into May's shinning sapphire eyes "I missed you to May" Ash said.

"You know Ash, I hated traveling without you" She confessed to you.

"You did?" Ash asked her.

"Yeah, Drew would always try to make advances on me and he tried to force himself on me, Harley got even worse" She said as she remembered at how awful Drew and Harley were.

Ash gave May a empathetic look "I'm sorry to hear that May" He said to her.

He honestly wanted to kick the shit out of Drew, trying make advances on him, I mean May did have an amazing body, but that doesn't give you the right to force yourself on her.

May then wrapped Ash into a hug as Ash blushed as he breasts were pressing against his chest, The two stayed silent for a few seconds just enjoying each other's company and gazing up at the stars, But soon they began sharing some more old and new stories, as they shared some laughs with each other.

May though could feel her self, getting tired as she let out a yawn "You tired?" Ash asked her.

"A little" She said softly gigging.

"Umm...Ash can you sleep with me tonight?" She asked nervously as she blushed.

Ash blushed as well from the question that she asked "Sure" Ash said.

May wasn't doing this to make Serena mad, but she missed Ash so much and she wanted to spend as much time with him as possible, The two then went into the guest room, where May was sleeping and the two of them got into bed and both of them were nervous, as it would be their first time sleeping together in awhile, In Hoenn and Kanto they had only slept a couple of time together and it was because May had nightmares and she went to Ash to comfort her.

"Night Ash" She said.

"Night May" He said.

May then cuddled up next to him and Ash's heart was beating, as her big breasts were pressing up against his chest and also her bottom was on his clothed boner as he was getting hard as his mind raced with dirty thoughts about May, He tried to think of different things, but he couldn't as he could think about was May and sexual fantasies.

Sweat was pouring from him and he hoped May didn't feel his boner poking through his boxers, He couldn't stop thinking about May and he couldn't fall asleep, May then wrapped her arms around him "Ash" She said his name in her sleep.

Ash then looked at May's face and she looked so cute sleeping and he just stared at her beautiful face, until he eventually feel asleep in May's arms.

Next Moring Ash's Room

Serena woke up the next morning, She noticed a empty spot next to her in the bed and she figured that Ash was downstairs eating breakfast. Serena then went into the bathroom and she took a shower and then got dressed and went downstairs, where she saw Delia, but she didn't see neither Ash or May in the dinning "Hey Delia where's Ash?" She asked his mother.

Delia softy giggled as she thought about the cute sight of seeing Ash and May sleeping together "Ash is in the guest room, sleeping with May" She replied.

Hearing this, made Serena fume on the inside with jealousy, Her boyfriend was sleeping with another women, and a beautiful women at that, "He is?" Serena asked as she tried to hide her rage from Delia.

Delia giggled again "Yeah, you should have seen them, they looked so adorable" Delia said.

Serena this quickly made her way upstairs, leaving Delia by herself, she could tell that Serena was angry and jealous and Delia could understand her jealousy, but Delia knew that May had no intent of making Serena jealous, as May missed Ash dearly and just wanted to spend some time with her old friend.

She wouldn't tell Serena this, but Delia always wanted to Ash to be with May, she didn't hate Serena, but she just wanted her son to date May more. May was sweet, kind, and very compassionate person and her and Ash had a lot in common and he knew Ash would be in great hands, She just wished Ash wasn't as dense as he was when he traveled with May.

As May made it quite clear that she liked Ash and she honestly felt bad for the poor girl, as Ash knew nothing about girls and May wanted to tell him so bad that she loved him, but alas she was afraid of getting her heart-broken or lose a great friend in Ash. May had come to Delia about how to confess her feelings for Ash and Delia tried her best of telling how May she could confess her love, but Ash was just to dense for his own good.


End file.
